Short Term Rental Pros Podcast

Hospitality.FM
Hospitality.FM
  • 5.0 (9)
  • Entrepreneurship
  • Updated Weekly

The Short Term Rental Pro Podcast is dedicated to sharing knowledge, experiences, and actionable takeaways from those who have built successful short-term rental and Airbnb businesses. STR Pro aims to inspire and educate the next generation of successful STR investors. Our host, Jeremy Werden is the founder of several 6 and 7-Figure short-term rental businesses. Jeremy has a 25 listing Airbnb portfolio that brings in over $1,000,000 a year and has done so through using multiple Airbnb / short-term rental strategies such as buying properties, managing (a.k.a “co-hosting”), renting and subletting (a.k.a “rental arbitrage”), and glamping. He has built this business from the ground up in only a short couple of years. He also has a 7 unit boat rental fleet. In order to scale these businesses Jeremy has had to leverage other people’s money (OPM) and financing which he talks about during podcast episodes. Jeremy also is the Co-Founder of BNBCalc, the premiere software for analyzing and under-writing short-term rental investments that has thousands of users. He also started the BNBPro Mastermind, a tight-knit community of hosts building their Airbnb empires together. Jeremy regularly posts on social media and also received more than 50M views across platforms. Each episode, we delve into the stories and experiences of successful short-term rental hosts, and get insights on how they built their businesses from the ground up. We also talk to service providers who have built innovative tools that are helping hosts automate or enhance their businesses. Whether you're a seasoned short-term rental host or just starting out, this podcast is packed with valuable tips and strategies to help you grow your business and achieve success. Feel free to reach out to Jeremy on Instagram @jeremywerden

  1. 2d ago

    Building a $37K Land Deal Into a Viral Airbnb

    In this episode of the Short-Term Rental Pros Podcast, host Jeremy Werden sits down with Rajan Chida, a 22-year-old entrepreneur and real estate developer documenting his journey of building a short-term rental development from the ground up. Rajan's journey started far outside traditional real estate. While in college, he built a successful shoe-flipping business, saving aggressively until he was able to purchase his first investment property at just 21. Soon after, a partnership with his longtime friend Renzo led him to a much bigger challenge: purchasing 2.5 acres in Virginia for $37,000 and developing a four-unit short-term rental project called Royal Oak Retreat—despite having virtually no development experience. What makes Rajan's story even more interesting is how he has built the entire journey in public. His social following grew from roughly 20,000 followers to more than 185,000, allowing him to attract contractors, mentors, investors, creators, and opportunities simply by documenting the process. Jeremy and Rajan break down what it's really like to develop an STR from scratch, build an audience, and turn attention into a potential business advantage. In this episode, you'll learn: How Rajan went from shoe flipping to real estate investing How he found and evaluated the $37K land opportunity Building a short-term rental development with little prior experience How building in public attracted contractors and experienced mentors The social media hooks and storytelling strategies behind his growth Why documenting the journey can be more powerful than simply promoting the finished product How to use social media to build an audience around a real estate project The challenges of getting financing as young developers Why testing one STR before building an entire development can reduce risk How Rajan plans to turn Royal Oak Retreat into a standalone brand Designing a health-focused guest experience with amenities like saunas, cold plunges, hot tubs, and wellness products Why understanding your unique story and audience can become a competitive advantage Whether you're an aspiring real estate investor, Airbnb host, STR developer, content creator, or entrepreneur, this episode offers a behind-the-scenes look at what happens when you combine real estate, hospitality, social media, and the willingness to build in public. Save Your Spot! Join Our Lakefront Retreat at Hyco Lake Mastermind: https://www.investstr.com/lake-front-retreat Property Management Mastermind: str-pros.com Need help buying a property: investstr.com Save 25% on BNB Calc. Use our exclusive discount through the link below: ⁠https://bnbcalc.com?fpr=strpros⁠

  2. Aug 12

    How to Build a Viral Airbnb: Direct Bookings, Social Media & Scaling STRs

    In this episode of the Short-Term Rental Pros Podcast, host Jeremy Werden sits down with three standout STR operators and creators: Rajan Chida, Kyle Miklasz, and Ryan Shapiro for an unfiltered conversation about building, marketing, and scaling short-term rental businesses. Rajan Chida shares the story behind Royal Oak Retreat, a luxury cabin project he launched while still in college. After purchasing land for $37,000 and building the first cabin for roughly $380,000 all-in, Rajan has used social media storytelling and influencer marketing to drive significant direct bookings. He also breaks down what he's learned about identifying the right audience, building a personal brand, and turning attention into actual revenue. Kyle Miklasz, founder of Big Sky Barn House and Wild Wild Warehouse, shares how he has built a portfolio of unique Airbnb destinations across eight states. His strategy is anything but traditional—transforming abandoned barns and warehouses into one-of-a-kind experiential stays. Kyle discusses the launch of his latest property in rural Iowa, which generated nearly $300,000 in gross bookings within its first eight weeks, and explains how he uses social media as another distribution channel for his properties. Ryan Shapiro, co-host of the Short-Term Rental Pros Podcast and a luxury co-hosting operator in Northeast Florida, joins the conversation to share his perspective on experiential stays, property management, and the realities of operating a growing STR portfolio. Together, Jeremy, Rajan, Kyle, and Ryan dive into what it really takes to turn unique properties into high-performing short-term rentals. In this episode, you'll learn: How to use social media to generate direct bookings Why having the right audience matters more than follower count How influencer marketing can drive bookings—and where it falls short Building unique STRs in markets that aren't traditional vacation destinations How to design properties with virality and guest experience in mind When it's time to hire help and build operational systems The growing pains that come with scaling an STR portfolio Why operators need to focus on their strengths and delegate the rest How direct bookings can reduce reliance on OTAs The real challenges behind running multiple short-term rentals Whether you're an Airbnb host, property manager, real estate investor, co-host, or aspiring STR entrepreneur, this episode offers a candid look at what it takes to build properties people actually want to book—and a business that can scale beyond the founder. This isn’t a conference. It’s a mastermind. Three days. A small group of STR founders, hosts, and brand builders. Real numbers, real playbooks, and real conversations you won’t find online. Bring your biggest bottleneck. Leave with a plan — and a room of people who will hold you accountable. 🌊 A lakefront retreat, not a conference room. 👉 Apply for a spot: https://www.investstr.com/lake-front-retreat 🎁 Save 25% on BNB Calc Want to make smarter decisions when analyzing potential short-term rental investments? BNB Calc helps STR investors analyze properties and estimate their potential returns. Use our exclusive 25% off discount through the link below: https://bnbcalc.com?fpr=strpros

  3. Aug 4

    Master Class on How to Create Social Media Content with Rajan Chida

    What separates creators who consistently grow from those who struggle to get views? In this episode of the STR Pros Podcast, host Ryan Shapiro sits down with content creator and social media strategist Rajan Chida to break down the strategies behind creating content that captures attention, builds trust, and drives business growth. Rajan shares the exact frameworks he's used to grow on social media, including how to find your niche, craft hooks that stop the scroll, document your journey, and turn everyday business moments into engaging content. He also explains why quality beats quantity, how to test different hooks using Trial Reels, and the mindset required to build a long-term personal brand. Whether you're an Airbnb host, short-term rental operator, entrepreneur, real estate investor, or anyone looking to grow a business online, this episode is packed with actionable advice you can apply immediately. In this episode, you'll learn: How to choose a niche without limiting your future growth The anatomy of a high-performing social media hook Why documenting your journey is more effective than trying to go viral How to test content ideas before publishing The importance of storytelling and audience retention How to create engaging videos using only your smartphone Why quality consistently outperforms quantity How to build a recognizable personal brand through consistent messaging Common mistakes creators make—and how to avoid them If you're looking to grow your audience, attract more customers, and build a brand through content, this conversation with Rajan Chida is a master class you won't want to miss. Follow the STR Pros Podcast for more conversations with the entrepreneurs, operators, and industry leaders shaping the future of short-term rentals and modern business.

  4. Jul 31

    What does the future of short-term rentals look like—and how can hosts stay ahead?

    In this episode of the STR Pros Podcast, Jeremy sits down with Leo Walton, Co-Founder of Truvi (formerly Superhog), one of the most respected voices in the short-term rental industry. Before co-founding Truvi, Leo helped grow onefinestay from a single luxury rental in London into a global vacation rental brand. Today, he works with property managers and vacation rental operators around the world to help them reduce risk, build trust with guests, and grow more resilient businesses. Together, Jeremy and Leo explore the future of the STR industry—from direct bookings and revenue management to AI, guest screening, and hospitality technology. They discuss why understanding your ideal guest is one of the biggest competitive advantages in today's market, how operators can build systems that scale, and why successful businesses focus on solving real operational challenges instead of chasing every new trend. In this episode, you'll learn: Why direct bookings are becoming a competitive advantage How AI is shaping the future of short-term rentals Smarter revenue management strategies for growing portfolios The importance of guest screening and risk management How understanding your ideal guest improves pricing and marketing Building systems that scale with your business Lessons from operating and serving vacation rental businesses globally Where the STR industry is headed over the next few years Whether you're an Airbnb host, co-host, vacation rental owner, property manager, or real estate investor, this episode is packed with practical insights to help you build a stronger, more profitable, and future-ready short-term rental business.

  5. Jul 29

    How Ryan Shapiro Scaled From 10 to 30+ STR Properties & $300K+ in Monthly Bookings

    How do you scale from managing fewer than 10 short-term rentals to 30+ properties—and more than $300K in monthly gross bookings? In this episode of the STR Pros Podcast, host Jeremy sits down with Ryan Shapiro to unpack Ryan’s journey of building and scaling his short-term rental property management business. Ryan shares how he went from getting his first listings and leaving his job to managing a growing portfolio of 30+ properties. He and Jeremy discuss the strategies, systems, delegation, and mindset shifts that helped make that growth possible—and why scaling successfully isn't always about adding as many properties as possible. They also dive into one of the biggest lessons they've learned in the STR industry: quality inventory matters. From Airbnb arbitrage and co-hosting to building operational systems and choosing properties that create memorable guest experiences, Jeremy and Ryan share practical insights for anyone looking to build a more profitable and sustainable short-term rental business. In this episode, you'll learn: • How Ryan scaled from fewer than 10 to 30+ STR properties• What helped his portfolio reach $300K+ in monthly gross bookings• Why mastering the basics is still one of the best ways to grow• How to delegate guest messaging, maintenance, and daily operations• Why 20% of your properties can create 80% of your headaches• When it makes sense to walk away from difficult properties• The pros and cons of Airbnb rental arbitrage• Why quality inventory can matter more than total unit count• How Ryan approaches luxury co-hosting in Florida• How systems and the right team can help you scale without handling everything yourself Whether you're an Airbnb host, STR investor, co-host, or property manager, this episode is packed with lessons for building a short-term rental business that can grow without taking over your life. Subscribe to the STR Pros Podcast for more conversations with Jeremy and other STR operators about Airbnb investing, co-hosting, property management, vacation rentals, operations, and scaling a profitable short-term rental business.

  6. 11/20/2024

    Jordan designed 300 Airbnbs in two years

    Jordan McDonough is a Co-Founder of Somerled Designs (a short term rental design company). Her and Jeremy sit down and have a convo about how she has helped build a design power-house with 60 employees in two years. Learn how she built her company and how her clients are having success launching high-potential Airbnb's.

  7. 11/13/2024

    Behind the Man Behind The Stays Experiential Hospitality Podcast. Meet Zach from Journey

    In this episode of the Short Term Rental Pros Podcast, Jeremy welcomes guest Zach, who shares his unique perspective on short-term rentals and his recent transition into a new role with Journey, a next-generation loyalty program. Zach discusses the acquisition of his previous company, Stay Watched, by Journey, and sheds light on the new platform's vision of combining vacation rentals and boutique hotels into a unified loyalty program. They delve into the importance of crafting unique, luxurious, and high-value experiences for guests, the shifting landscape of consumer expectations towards luxury, and the significant role of social media in direct marketing for short-term rentals. Key takeaways include building a strong hospitality brand, leveraging social proof, and focusing on fewer but highly differentiated units to create exceptional guest experiences.

  8. 10/23/2024

    Navigating Challenges and Triumphs: Hurricanes, High-Profile Events, and Industry Insights

    In this comprehensive episode of the Short Term Rental Pros podcast, Jeremy recounts a period filled with remarkable events and significant challenges. From dealing with the aftermath of two hurricanes affecting properties in Florida and North Carolina, to attending the Chicago Marathon and VRMA conference, Jeremy shares personal stories and key lessons on resilience, the importance of flood insurance, and community support. The episode highlights insights from major conferences discussing networking, AI, and short-term rental software innovations. Additionally, it delves into the creation and growth of BNBCalc, a tool aimed at enhancing short-term rental portfolios, and the ambitions behind it. Jeremy also reflects on his encounters with major companies and a high-profile interview involving Tim Walz, navigating logistics with the Secret Service. Moving between personal anecdotes, industry advancements, and future aspirations, the episode underscores the power of mission-driven investments, consistency, and seizing unique opportunities in the rental industry.

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5
out of 5
9 Ratings

About

The Short Term Rental Pro Podcast is dedicated to sharing knowledge, experiences, and actionable takeaways from those who have built successful short-term rental and Airbnb businesses. STR Pro aims to inspire and educate the next generation of successful STR investors. Our host, Jeremy Werden is the founder of several 6 and 7-Figure short-term rental businesses. Jeremy has a 25 listing Airbnb portfolio that brings in over $1,000,000 a year and has done so through using multiple Airbnb / short-term rental strategies such as buying properties, managing (a.k.a “co-hosting”), renting and subletting (a.k.a “rental arbitrage”), and glamping. He has built this business from the ground up in only a short couple of years. He also has a 7 unit boat rental fleet. In order to scale these businesses Jeremy has had to leverage other people’s money (OPM) and financing which he talks about during podcast episodes. Jeremy also is the Co-Founder of BNBCalc, the premiere software for analyzing and under-writing short-term rental investments that has thousands of users. He also started the BNBPro Mastermind, a tight-knit community of hosts building their Airbnb empires together. Jeremy regularly posts on social media and also received more than 50M views across platforms. Each episode, we delve into the stories and experiences of successful short-term rental hosts, and get insights on how they built their businesses from the ground up. We also talk to service providers who have built innovative tools that are helping hosts automate or enhance their businesses. Whether you're a seasoned short-term rental host or just starting out, this podcast is packed with valuable tips and strategies to help you grow your business and achieve success. Feel free to reach out to Jeremy on Instagram @jeremywerden

Information

  • Channel
    Hospitality.FM
  • Creator
    Jeremy Werden
  • Years Active
    2023 - 2026
  • Episodes
    77
  • Rating
    Explicit
  • Copyright
    © Jeremy Werden

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